Sodium Iodide → HCID 11637522, compound

HRID 1921331Notes

Reaction equation

HRID 1921331 reaction equation
C[O:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])=[C:5]([CH3:21])[N:4]=1.[I-].[Na+].Cl[Si](C)(C)C.C(#N)C>O>[CH3:21][C:5]1[NH:4][C:3](=[O:2])[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]=1[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 67492493HCID 67492493, compound

Product 1

HCID 11637522HCID 11637522, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 3-(1-methoxy-3-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrile (56 mg, 0.2 mmol), sodium iodide (60 mg, 0.4 mmol), chlorotrimethylsilane (51 μL, 0.4 mL) and acetonitrile (3 mL) is heated at reflux temperature for 1.5 hr. The cooled reaction mixture is diluted with water (5 mL) and the solids are collected by filtration to give 3-(3-methyl-1-oxo-1,2,5,6,7,8-hexahydroisoquinolin-4-yl)benzonitrile (45 mg, 87%) as a beige solid. LC/MS: MS m/e=265 (M+H); RT 2.97 min.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1.5 hr
  3. customThe cooled reaction mixture
  4. filtrationthe solids are collected by filtration

Sources & evidence

ORD record
ord-5437c6296f884da595b6e34672eb8062
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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